As a process for producing optically active nitroalcohols by nitroaldol reactions using an asymmetric catalyst, for example, there has been reported that optically active nitroalcohols are obtained with satisfactory results in chemical yield and asymmetric yield by reactions of aldehydes and nitroalkanes using an asymmetric catalyst composed of optically active binaphthols, rare earth metal compounds, and alkali metal compounds (See Japanese Unexamined Patent Application Publication Nos. 6-154618, 9-253502, and 9-255631, J. Am. Chem. Soc. vol. 114, p. 4418 (1992), Tetrahedron Letters, vol. 34, p. 855 (1993), and J. Org. Chem., vol. 60, p. 7388 (1995)).
There has also been reported that optically active nitroalcohols can be obtained by reactions of aldehydes and nitroalkanes using an asymmetric catalyst consisting of optically active binuclear zinc complexes (See, U.S. Pat. No. 6,610,889, and Angew. Chem. Int. Ed., vol. 41, p. 861 (2002)).
However, these processes have problems in that the reactions are required to be carried out for a long period of reaction time, and also equipments for low temperature reactions and a large amount of expensive asymmetric ligands or rare earth metal compounds are required. The methods described in U.S. Pat. No. 6,610,889, and in Angew. Chem. Int. Ed., vol. 41, p. 861 (2002) also have a problem in that the addition of molecular sieves is required, however these methods are not sufficient for practical use.